Schiff base pyridoxal-pyridoxamine | 122908-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Schiff base pyridoxal-pyridoxamine
• 英文别名: N-pyridoxylidenepyridoxylamine；pyridoxyl-pyridoxyliden-amine；Pyridoxyl-pyridoxyliden-amin
• CAS: 122908-64-9
• 化学式: C₁₆H₁₉N₃O₄
• 分子量: 317.345
• InChiKey: ADDANUZRAMQVBU-YAXRCOADSA-N

物化性质

• 熔点：
  235 °C
• 沸点：
  713.3±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  119.06
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Schiff base pyridoxal-pyridoxamine 、 二正丁基氧化锡 以 乙醇 、 甲苯 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Diorganotin(IV)-promoted deamination of amino acids by pyridoxal: SnR22+ complexes of pyridoxal 5′-phosphate and of the Schiff base pyridoxal-pyridoxamine (PLPM), and antibacterial activities of PLPM and [SnR2(PLPM-2H)] (R=Me, Et, Bu, Ph)

  摘要：

  Pyridoxal 5'-phosphate (PLP) and pyridoxal (PL) itself were reacted with diorganotin(IV) derivatives in the presence and absence of aminoacids. With PLP the complexes [SnR2(PLP-2H)] (R = Me, Et, Bu) were isolated and characterized by EI and FAB mass spectrometry and by IR, Raman and Mossbauer spectroscopy. Reaction mixtures containing PL, valine or glycine and SnR2(OAc)(2) (R = Me, Et) afforded complexes of the form [SnR2(PLPM-2H)], where PLPM is the Schiff base formed by condensation of PL and pyridoxamine (PM). PM was presumably formed by transamination between valine or glycine and PL. The PLPM complexes, and their butyl and phenyl analogues, were also synthesized directly by reacting SnR2O and PLPM, and were characterized by El and FAB MS, by IR, Raman, Mossbauer and NMR spectroscopy, and in the case of the methyl and ethyl compounds by single-crystal, X-ray diffractometry. Crystals of [SnMe2(PLPM-2H)].H2O and [SnEt2(PLPM-2H)] consist of molecules in which the ligand is bound to the metal through the O atoms of the two deprotonated phenolic hydroxyl groups and the iminic N atom, and the metal exhibits distorted square pyramidal coordination. Both PLPM and its complexes show intense antibacterial activity against Pseudomonas aeruginosa (ATCC27853), but only the complexes exhibit significant activity against the other four bacterial strains assayed, Staphylococcus aureus, Bacillus subtilis, Escherichia coli and a carbapenem-resistant P. aeruginosa strain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(02)01331-1
• 作为产物：
  描述：

  pyridoxamine dihydrochloride 、 吡哆醛盐酸盐 在 氢氧化钾 作用下， 反应 0.5h， 以80%的产率得到Schiff base pyridoxal-pyridoxamine
  参考文献：
  名称：

  X = y-zh系统作为潜在的1,3-偶极子：第22部分。1吡ido醛亚胺的环加成反应。与α-氨基酸外消旋和转氨酶有关。

  摘要：

  在乙腈，甲苯或二甲苯中加热时，∞-氨基酸酯和相关胺的乙二醛亚胺会与N-苯基马来酰亚胺发生环加成反应。环加成以良好的产率进行，具有立体定向性，并涉及内过渡态。假定反应性中间体是通过原生质体从亚胺立体定向产生的NH甲亚胺基亚胺。

  DOI：

  10.1016/s0040-4020(01)86100-7

文献信息

• X=Y-ZH systems as potential 1,3-dipoles. Activation of the ZH proton in imines
  作者：R. Grigg、H.Q.N. Gunaratne、V. Sridharan、S. Thianpatanagul、M. Tute

  DOI：10.1016/s0040-4039(00)88342-2

  日期：1983.1

  A range of substituents is capable of inducing thermal 1,3-dipole formation in imines by activation of the CH proton as shown by trapping experiments with dipolarophiles.

  一系列取代基能够通过激活CH质子而在亚胺中诱导热1，3-偶极子形成，如用双亲性试剂进行的捕获实验所示。
• Chemistry of Vitamin B₆. VII. Pyridoxylidene- and Pyridoxylamines¹
  作者：Dorothea Heyl、Eileen Luz、Stanton A. Harris、Karl Folkers

  DOI：10.1021/ja01191a038

  日期：1948.11
• GRIGG, R.;GUNARATNE, H. Q. N.;SRIDHARAN, V.;THIANPATANAGUL, S.;TUTE, M., TETRAHEDRON LETT., 1983, 24, N 40, 4363-4366
  作者：GRIGG, R.、GUNARATNE, H. Q. N.、SRIDHARAN, V.、THIANPATANAGUL, S.、TUTE, M.

  DOI：——

  日期：——
• GRIGG, RONALD;THIANPATANAGUL, SUNIT;KEMP, JAMES, TETRAHEDRON, 44,(1988) N 23, C. 7283-7292
  作者：GRIGG, RONALD、THIANPATANAGUL, SUNIT、KEMP, JAMES

  DOI：——

  日期：——
• Diorganotin(IV)-promoted deamination of amino acids by pyridoxal: SnR22+ complexes of pyridoxal 5′-phosphate and of the Schiff base pyridoxal-pyridoxamine (PLPM), and antibacterial activities of PLPM and [SnR2(PLPM-2H)] (R=Me, Et, Bu, Ph)
  作者：José S Casas、Alfonso Castiñeiras、Félix Condori、Marı́a D Couce、Umberto Russo、Agustı́n Sánchez、Rafael Seoane、José Sordo、José M Varela

  DOI：10.1016/s0277-5387(02)01331-1

  日期：2003.1

  Pyridoxal 5'-phosphate (PLP) and pyridoxal (PL) itself were reacted with diorganotin(IV) derivatives in the presence and absence of aminoacids. With PLP the complexes [SnR2(PLP-2H)] (R = Me, Et, Bu) were isolated and characterized by EI and FAB mass spectrometry and by IR, Raman and Mossbauer spectroscopy. Reaction mixtures containing PL, valine or glycine and SnR2(OAc)(2) (R = Me, Et) afforded complexes of the form [SnR2(PLPM-2H)], where PLPM is the Schiff base formed by condensation of PL and pyridoxamine (PM). PM was presumably formed by transamination between valine or glycine and PL. The PLPM complexes, and their butyl and phenyl analogues, were also synthesized directly by reacting SnR2O and PLPM, and were characterized by El and FAB MS, by IR, Raman, Mossbauer and NMR spectroscopy, and in the case of the methyl and ethyl compounds by single-crystal, X-ray diffractometry. Crystals of [SnMe2(PLPM-2H)].H2O and [SnEt2(PLPM-2H)] consist of molecules in which the ligand is bound to the metal through the O atoms of the two deprotonated phenolic hydroxyl groups and the iminic N atom, and the metal exhibits distorted square pyramidal coordination. Both PLPM and its complexes show intense antibacterial activity against Pseudomonas aeruginosa (ATCC27853), but only the complexes exhibit significant activity against the other four bacterial strains assayed, Staphylococcus aureus, Bacillus subtilis, Escherichia coli and a carbapenem-resistant P. aeruginosa strain. (C) 2002 Elsevier Science Ltd. All rights reserved.